Oxygen- and Sulfur-Containing Positively Charged Polycyclic Aromatic Hydrocarbons

Benzo[5,6]naphthaceno[1,12,11,10-jklmna]xanthylium (BNAX) and benzo[5,6]naphthaceno[1,12,11,10-jklmna]thioxanthylium (BNATX) salts were synthesized. Comparison of the UV−vis absorption and emission spectra of them and dibenzo[jk,mn]naphtho[2,1,8-fgh]thebenidinium (DBNT) salts suggests that the incor...

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Bibliographic Details
Published inOrganic letters Vol. 11; no. 24; pp. 5686 - 5689
Main Authors Wu, Dongqing, Pisula, Wojciech, Haberecht, Monika C, Feng, Xinliang, Müllen, Klaus
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.12.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PYRYLIUM
DEHYDRONIUM COLOR SUBSTANCES
SALTS
LIQUID-CRYSTALS
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Summary:Benzo[5,6]naphthaceno[1,12,11,10-jklmna]xanthylium (BNAX) and benzo[5,6]naphthaceno[1,12,11,10-jklmna]thioxanthylium (BNATX) salts were synthesized. Comparison of the UV−vis absorption and emission spectra of them and dibenzo[jk,mn]naphtho[2,1,8-fgh]thebenidinium (DBNT) salts suggests that the incorporation of different heteroatoms in the same PAH core changes their optoelectronic properties profoundly. Ordered columnar liquid crystalline phases were observed for di- and tridodecyl-substituted BNAX salts. X-ray scattering and molecular modeling indicate that three BNAX molecules self-assemble into a disklike structure, which further organizes into hexagonal columnar phases.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol902366y